Since the expanded format in 1997, a PDL team has failed to reach the Third Round just five times (1998, 2002, 2007, 2008, 2010). The recent struggles can be attributed to the fact that in 2007, the format was changed so that all non-MLS teams began the tournament in the First Round, unlike previous tournaments where PDL teams were matched up with USASA or other PDL clubs.
The biggest rout in the Third Round during the Professional Era came in 2003, when the Virginia Beach Mariners (A-League, 2nd Division) defeated the Carolina Dynamo (3rd Division) 5-0. Dante Washington and Roland Aguilera both scored twice for the Mariners.
In their 1998 Third Round match, Major League Soccer’s Tampa Bay Mutiny and the Worcester Wildfire of the A-League combined for nine cautions, and saw four players sent off. Tampa Bay won the match on penalties, after finishing extra time drawn 2-2.
The highest scoring Professional Era Open Cup game occurred in the Third Round on July 19, 2005 when the Richmond Kickers (USL-1) defeated the Ocean City Barons (PDL) 8-4. The game was played at Sports Backers Stadium in Richmond, Va., a week after the original match was re-scheduled due to bad weather. The Barons scored first in the 4th minute, but Richmond stormed back with four goals in less than 20 minutes. With the score 4-1, Ocean City scored a pair of goals on either side of halftime to cut the lead to one. At that point, Neil Holloway, the Barons player/manager made some offensive-minded substitutions and pushed for the equalizer, but at that point, the flood gates opened and Richmond scored four more in the second half. The game would finish 8-4. The previous total goals record was shared by a pair of games. In 1995, the Seattle Sounders (A-League, now USL-1) defeated the Everett BigFoot (USISL Pro, now USL-2) 9-2 and in 1999 the San Diego Flash (A-League) cruised past the Arizona Sahuaros (D3 Pro, 3rd Division) by the same score.
In 2007, a record five MLS teams were upset in the Third Round, with only three clubs advancing to the next round. It was the fewest MLS teams to enter the Quarterfinals in the Modern Pro Era.
On five occasions, a pair of 3rd Division clubs have won Third Round games in the same tournament. In 2007, the Richmond Kickers (1-0 win vs. Los Angeles Galaxy) and the Harrisburg City Islanders (1-0 win vs. DC United) were victorious. Two years later, in 2009, the Wilmington Hammerheads won another Third Round match (their fourth) and with the Harrisburg City Islanders, they were the second pair of USL-2 teams to reach the Quarterfinals in the same season. In 2010, the City Islanders made it two years in a row, upsetting the New York Red Bulls 1-0 in overtime, while the Charleston Battery (who moved down to the 3rd Division after several years in the 2nd Division) eliminated the Chicago Fire of MLS in a penalty kick shootout after a scoreless draw. In 2012, with the expanded tournament (64 teams), three clubs from the 3rd Division reached Round 4. The Harrisburg City Islanders erased a 3-0 deficit in the second extra time period, forced penalty kicks and upset the New England Revolution. The Charlotte Eagles knocked off FC Dallas 2-0, while the Dayton Dutch Lions surprised the Columbus Crew by winning the first ‘Ohio Derby’ by a score of 2-1. In 2013, Orlando City SC upset their first MLS team, knocking off the Colorado Rapids 3-1, while the Charleston Battery upset the San Jose Earthquakes 1-0.
In 2004, a Modern Pro Era record four amateur teams reached the Third Round. All four teams were from the PDL and all four of them lost by a single goal (three of them by golden goal) in their Round 3 matches:
* Boulder Rapids Reserve lost to the Minnesota Thunder (A-League, Division II) 2-1 in sudden death extra time
* Carolina Dynamo lost to the Atlanta Silverbacks (A-League, Division II) 3-2 in sudden death extra time
* Cape Cod Crusaders lost to the Richmond Kickers (A-League, Division II) 1-0 in sudden death extra time
* Chicago Fire Reserves lost to the Rochester Raging Rhinos (A-League, Division II) 1-0 in regulation.
In 2013, that record was matched with four new teams:
* Ocean City Nor’easters (PDL) lost 2-1 at Philadelphia Union (MLS)
* Des Moines Menace (PDL) lost 2-0 at Sporting Kansas City (MLS)
* Reading United (PDL) lost 2-0 at New York Red Bulls (MLS)
* FC Tucson (PDL) lost 2-0 at Houston Dynamo (MLS)
In 2006, four more amateur clubs reached Round 3, but for the first time, two of them advanced:
* Dallas Roma FC eliminated Chivas USA of MLS 4-2 in penalty kicks after playing to a scoreless draw to become the first USASA club to eliminate a Major League Soccer team.
* Carolina Dynamo defeated the Seattle Sounders (USL First Division, Division II) 3-2 after extra time
* Michigan Bucks lost to the Columbus Crew (MLS, Division I) 4-1
* Des Moines Menace lost to the Kansas City Wizards (MLS, Division I) 2-1
In 2012, for just the second time in the Modern Professional Era, two amateur teams advanced beyond Round 3, but both of them were particularly historic:
*The Michigan Bucks became just the fourth PDL team to eliminate a Major League Soccer team when they defeated the Chicago Fire 3-2 in extra time at the Ultimate Soccer Arenas in Pontiac, Mich. With the win, they also became the first amateur team to defeat multiple MLS teams in club history after they upset the New England Revolution in Foxboro in 2000.
* Cal FC, a USASA club from Southern California managed by former US international Eric Wynalda, not only became the first USASA team to score a goal against a Major League Soccer team, but they became the first to defeat one. (Dallas Roma FC won their game in PKs) Cal FC upset the Portland Timbers 1-0 in extra time at Jeld-Wen Field in Portland, Ore. Cal FC joined the Michigan Bucks as the only amateur team to defeat an MLS team on the road, but the Bucks’ upset of New England in 2000 remains the only time an amateur team has done it within 90 minutes.
In 2003, the Fresno Fuego (PDL) became the first amateur team to win a Third Round game in the Modern Professional Era (1995-present), upsetting the El Paso Patriots (A-League, Division II) by a score of 5-2.
Only seven 3rd Division clubs have ever won Third Round matches:
Wilmington Hammerheads (2003, 2006, 2007, 2009)
Harrisburg City Islanders (2007, 2009, 2010, 2012)
Charleston Battery (2010, 2013)
Richmond Kickers (2007, 2011)
Charlotte Eagles (2012)
Dayton Dutch Lions (2012)
Orlando City SC (2013)
San Francisco Bay Seals (1997)